Increase ester count with Hydrochloric acid?

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vqstatesman
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Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Hi All,

I have followed some of the threads regarding increasing ester count by using Sulphuric acid. I gave this a try a few months ago and am keenly waiting on my rum maturing and ageing before I sample and tell the difference.

Long before reading up on the threads where the likes of Der Wo talk about adding Sulphuric to finished wash or low wines I made a batch of rum that had more flavour than usual, it was a pure fluke/mistake at the time... I will elaborate as follows:

I was distilling a new batch of rum just after cleaning my plated column with Hydrochloric acid. I'm 100% certain no no Hydrochloric made it into my batch. I'm 100% certain that I had also fully rinsed my column and plates thoroughly. When making cuts I noticed that the flavour was amplified significantly, not different just amplified.

Was it the Hydrochloric acid (that was rinsed off anyway) that gave me the flavour boost? I'm not sure. Anyone wish to comment?

So my question is who has used Hydrochloric in their wash? Could this be used same as Der Wo uses Sulphuric?

Ps Der Wo if you do read this I wish to say a big thank you. All of your threads and comments are so full of detail, fact, curiosity and just plain old splender :)
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Saltbush Bill
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Re: Increase ester count with Hydrochloric acid?

Post by Saltbush Bill »

My guess is that it was diffferent becuase your still was spotlessly clean.....mine has been clean twice in 7-8 years.......was it really better or just different? I seem to remember Yummyrum doing a lot of experimentation with different acids long ago. Pretty sure he gave it away as the results were not worth the effort.
Could be wrong.
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Re: Increase ester count with Hydrochloric acid?

Post by decoy »

I am not one to be a scare monger, however....

I think this information needs to be discussed but induced addition of acids to a wash or distillation needs to be DISCOURAGED and/or stopped as DANGEROUS.

1. ACIDS can be distilled and transferred through vapor, this includes hydrochloric and sulfuric acid.

2. Esterification is a key component in every aspect of distillation, from the mash to still design and size.

google > "copper catalyzed esterification"

When fermenting a wash, depending on the type of bill, be it grain fruit or sugar will from start contain various fats and acids, these react in your boiler and are accelerated when heated.
Your boiler construction be it glass stainless or copper as well as the duration or dwell in the boiler before collection will have different effects or esterification conversion factors.
If the Acid is not converted it can be transferred via vapor into you final product.
This will also etch or corrode copper and lead free solder well above what would occur under normal distillation, if the lead free solder or copper is in the downhill path like condensers, the heavy metals as well as acids will end up in your product.

My simple answer is to stick with natural processes unless you have means of testing the final product, like gas chromatography.

Cheers
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Re: Increase ester count with Hydrochloric acid?

Post by rubelstrudel »

I disagree Decoy. Acids aren't that scary things. Especially not in the concentrations we're talking about here. Anyway, if the acids do get through the distillate will taste sour... it is a basic property of acids.

Some addition of a strong acid such as Sulfuric acid should act as a catalyst in the transformation of carboxylic acids already in your wash and alcohols into esters. Wether or not it makes any difference whatsoever to add a few cl of sulfuric acid in a large 25L batch of wash is another matter.

To get instant esterification like we do in science class in high school you'd need concentrated sulfuric, and water free alcohols and carboxylic. With more than 10% water the reaction will no longer be instant and esterification will require heat and time to happen. The wash will be 89-90% water.

Now, my guess is that it is not the lack of a catalyst that hinders esterification in your dunder, but rather the lack of carboxylic acids and alcohols. So adding muriatic acid, butyric acid, propionic acid, iso-butyric acid among others and some alcohols (methanol, propanol, butanol etc) from the feints have a much higher likelihood of actually making more esters. After all, that's what esters are made from, and if you don't have them - there will be no esters.

Adding all that stuff into your wash, it will stink.... But hopefully running the still in full reflux for a while will coax the alcohols and acids to esterify. I haven't really tried yet. Getting my hands on the acids is more difficult (or expensive) than I thought it would be.
Always impatient. But learning.
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Re: Increase ester count with Hydrochloric acid?

Post by Yummyrum »

Saltbush Bill wrote: I seem to remember Yummyrum doing a lot of experimentation with different acids long ago. Pretty sure he gave it away as the results were not worth the effort.
Could be wrong.
My play with Hydrochloric acid was nothing to do with esters . It was part of an experiment about clarifying wash using calcium hydroxide to settle out solids ... the HCl was to raise the pH back to 5ish for fermentation . ... also ... there was some rumour that Bundy used Hydrochloric acid .... although I have never heard where or why it was used :econfused:

But yeah , no magic bullet from me using HCl ..... but wasn't using it to chase esters
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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Small quantity 0.1% of your wash or low wines, personally I don't see this as dangerous.

Both the Hydrochloric and Sulphuric acids are commonly used in food production.
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Re: Increase ester count with Hydrochloric acid?

Post by CuWhistle »

From the Parent Site: Grain / Mashing. https://homedistiller.org/grain/wash-grain/mashing
"Jack warns ...
few of the books on brewing/distilling say that weak sulfuric acid can be used to drop the Ph of grain mashes. According to the e-chapters you sent me, and the Seagram's distilling textbook I have:THE PRESENCE OF SULFURIC ACID DIRECTLY RESULTS IN THE FORMATION OF ETHYL CARBONATE IN THE FINAL SPIRIT!!!- THIS CHEMICAL IS A KNOWN CARCINOGEN AND IT'S PRESENCE IS RESTRICTED BY ALL GOVERNMENTS IN SPIRITS CONSUMED BY HUMANS!! I've always used lactic acid (or backset) for adjusting Ph in my beers ,etc.- I'm glad I've never used sulfuric acid.
"
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Re: Increase ester count with Hydrochloric acid?

Post by shaawnzee »

CuWhistle wrote:From the Parent Site: Grain / Mashing. https://homedistiller.org/grain/wash-grain/mashing
"Jack warns ...
few of the books on brewing/distilling say that weak sulfuric acid can be used to drop the Ph of grain mashes. According to the e-chapters you sent me, and the Seagram's distilling textbook I have:THE PRESENCE OF SULFURIC ACID DIRECTLY RESULTS IN THE FORMATION OF ETHYL CARBONATE IN THE FINAL SPIRIT!!!- THIS CHEMICAL IS A KNOWN CARCINOGEN AND IT'S PRESENCE IS RESTRICTED BY ALL GOVERNMENTS IN SPIRITS CONSUMED BY HUMANS!! I've always used lactic acid (or backset) for adjusting Ph in my beers ,etc.- I'm glad I've never used sulfuric acid.
"
I cannot find a single thing online saying monoethyl carbonate is a carcinogen. In fact, I found several references saying it's naturally occurring in alcoholic beverages and wine.

Diethyl carbonate is used as a solvent in some intramuscular injections...so, benign.

Ethylene carbonate (which isn't even possible to form) is also quite benign.

Monoethyl carbonate will be easily hydrolyzed in the stomach (highly acidic) to carbonic acid/CO2 and ethanol. This molecule is harmless.

If sulfuric has anything to do with elevated levels of ethyl carbonate, it's not sulfuric dependent, just acid catalyzed. Also as previously stated, the large presence of water fights against ester formation simply from rxn of the components alone (that's where enzymes come into play from yeast).

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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

I do love this forum and the variety of everyones backgrounds and differing knowledge.

It's not about who's right or wrong it's great to see everyone contribute based on their knowledge, education, background or personal experience.

Let's keep the banter and debate going. Surely there are more members who wish to comment and debate?
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Re: Increase ester count with Hydrochloric acid?

Post by Saltbush Bill »

My two bobs worth.....if someone cant make a good tasting rum without filling the wash with acids and other strange ingredients they really need to look at the distillation and oaking/ aging methods they are using.
The KISS principle works for me.
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Re: Increase ester count with Hydrochloric acid?

Post by Yummyrum »

shaawnzee wrote:
CuWhistle wrote:From the Parent Site: Grain / Mashing. https://homedistiller.org/grain/wash-grain/mashing
"Jack warns ...
few of the books on brewing/distilling say that weak sulfuric acid can be used to drop the Ph of grain mashes. According to the e-chapters you sent me, and the Seagram's distilling textbook I have:THE PRESENCE OF SULFURIC ACID DIRECTLY RESULTS IN THE FORMATION OF ETHYL CARBONATE IN THE FINAL SPIRIT!!!- THIS CHEMICAL IS A KNOWN CARCINOGEN AND IT'S PRESENCE IS RESTRICTED BY ALL GOVERNMENTS IN SPIRITS CONSUMED BY HUMANS!! I've always used lactic acid (or backset) for adjusting Ph in my beers ,etc.- I'm glad I've never used sulfuric acid.
"
I cannot find a single thing online saying monoethyl carbonate is a carcinogen. In fact, I found several references saying it's naturally occurring in alcoholic beverages and wine.

Diethyl carbonate is used as a solvent in some intramuscular injections...so, benign.

Ethylene carbonate (which isn't even possible to form) is also quite benign.

Monoethyl carbonate will be easily hydrolyzed in the stomach (highly acidic) to carbonic acid/CO2 and ethanol. This molecule is harmless.

If sulfuric has anything to do with elevated levels of ethyl carbonate, it's not sulfuric dependent, just acid catalyzed. Also as previously stated, the large presence of water fights against ester formation simply from rxn of the components alone (that's where enzymes come into play from yeast).

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Shaawnzee... I believe that is a typo Ethyl Cabonate should have been Ethyl Carbomate .

Go do your reseach again .

It’s amazing how one little letter in a word makes a big difference
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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Saltbush Bill wrote:My two bobs worth.....if someone cant make a good tasting rum without filling the wash with acids and other strange ingredients they really need to look at the distillation and oaking/ aging methods they are using.
The KISS principle works for me.
I completely agree with this comment. If you can't master something good there is not point in trying to go next level or advanced mode.

I make fantastic rum and age it for 1-3 years before drinking and sharing. It's my signature and quite a nice drop.

I'm just up for some experimentation and chasing something different.

I've started down a few different rabbit holes lately just for the fun of it. I blame aged dunder for getting me started on this journey.
Last edited by vqstatesman on Fri Jun 28, 2019 11:57 pm, edited 1 time in total.
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Re: Increase ester count with Hydrochloric acid?

Post by NZChris »

Forums are great places for getting new ideas and directions, but not places for finding Gospel Truth about anything. When you find something new and interesting, (and especially if it is 'out there'), on the net, it pays to look up the science behind it before you take the bait.

Do "ETHYL CARBONATE" or "Ethyl Carbomate" really exist and, if they do, how are they relevant in a thread about hydrochloric acid and esters?
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Re: Increase ester count with Hydrochloric acid?

Post by CuWhistle »

Because the OP's first sentence talks about Sulfuric / Sulphuric acid.

Best advice apparently is to read, read, read. I was doing just that, to brush up on forgotten shit, and I read the quote on the parent site this morning and thought it relevant to this discussion. CARBONATE OR CARBOMATE. I'm not sure of the chemistry but I ain't never put nothin' like that in my washes so far and don't intend on doing so in the near future neither.
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Re: Increase ester count with Hydrochloric acid?

Post by Saltbush Bill »

I see you understood my comment completely VQ. :thumbup:
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Re: Increase ester count with Hydrochloric acid?

Post by decoy »

Saltbush Bill wrote:My two bobs worth.....if someone cant make a good tasting rum without filling the wash with acids and other strange ingredients they really need to look at the distillation and oaking/ aging methods they are using.
The KISS principle works for me.
+1

In my original response, my concerns were related to adding Acid's in an attempt to chase esters etc, not buffering your wash to achieve a desired PH, however when buffering your wash to reach a PH level consideration should be made as to the type of Acid or Alkaline used, always use buffers known to be safe for use in food preparation preferably with supporting technical documentation for their safe use.

Their is no magic chemical that will fix your failure to understand and follow a proven recipe and process.
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Re: Increase ester count with Hydrochloric acid?

Post by shaawnzee »

Yummyrum wrote:
shaawnzee wrote:
CuWhistle wrote:From the Parent Site: Grain / Mashing. https://homedistiller.org/grain/wash-grain/mashing
"Jack warns ...
few of the books on brewing/distilling say that weak sulfuric acid can be used to drop the Ph of grain mashes. According to the e-chapters you sent me, and the Seagram's distilling textbook I have:THE PRESENCE OF SULFURIC ACID DIRECTLY RESULTS IN THE FORMATION OF ETHYL CARBONATE IN THE FINAL SPIRIT!!!- THIS CHEMICAL IS A KNOWN CARCINOGEN AND IT'S PRESENCE IS RESTRICTED BY ALL GOVERNMENTS IN SPIRITS CONSUMED BY HUMANS!! I've always used lactic acid (or backset) for adjusting Ph in my beers ,etc.- I'm glad I've never used sulfuric acid.
"
I cannot find a single thing online saying monoethyl carbonate is a carcinogen. In fact, I found several references saying it's naturally occurring in alcoholic beverages and wine.

Diethyl carbonate is used as a solvent in some intramuscular injections...so, benign.

Ethylene carbonate (which isn't even possible to form) is also quite benign.

Monoethyl carbonate will be easily hydrolyzed in the stomach (highly acidic) to carbonic acid/CO2 and ethanol. This molecule is harmless.

If sulfuric has anything to do with elevated levels of ethyl carbonate, it's not sulfuric dependent, just acid catalyzed. Also as previously stated, the large presence of water fights against ester formation simply from rxn of the components alone (that's where enzymes come into play from yeast).

Sent from my SM-G965U using Tapatalk
Shaawnzee... I believe that is a typo Ethyl Cabonate should have been Ethyl Carbomate .

Go do your reseach again .

It’s amazing how one little letter in a word makes a big difference
Yummyrum,

Yet another typo... No such thing as carbomate... But we are on the right track with carbamate! Yes, ethyl carbamate is carcinogenic.

It's found in all fermented things from urea and ethanol. Seems that heat is a major factor, ie, toasted bread has more than untoasted.

Doesn't appear a lower pH plays a detrimental role however. Found this:

"For example, lowering the temperature during fermentation and storage, lowering the pH, lowering the ethanol content, and adding diammonium phosphate as a supplement minimize the EC concentration. However, most of these techniques are performed as auxiliary preventive methods, and some are even impossible to achieve in practical fermentation situations (Zhao and others 2013a). "

I encourage all interested to look at table4 (Methods to decrease ethyl carbamate in those fermented beverages whose main precursor is cyanic acid).

https://onlinelibrary.wiley.com/doi/ful ... 4337.12084" onclick="window.open(this.href);return false;" rel="nofollow

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Re: Increase ester count with Hydrochloric acid?

Post by CuWhistle »

No mention of sulphuric acid in that study. A good read though.
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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Was just reading through the parent site for a different reason but found this which I will quote:

"Ester formation in the still and during aging
Esters can form anytime an alcohol molecule is in the presence of an carboxylic acid and a catalytic acid. This is mainly attributed to Fischer Esterification. Fischer esterification increases as temperatures increase and with lower pH levels. This leads to a significant increase in ester formation during distillation. It may also be a contributing factor to the "Slow Distillation" movement to create a better product. In aging the ester formation process continues but at a slower pace as product is normally stored at room temperature. If stored in a wooden barrel tannic acid from the wood is absorbed into the product at it ages and it lowers the pH slowly. This acidity increases ester production. This leads to a more complex flavor profile. Doping ferments and low wines with small amount of strong acids, like sulfuric, increases the speed of this reaction. It is not recommended for the final product."

https://homedistiller.org/wiki/index.php/Ester" onclick="window.open(this.href);return false;" rel="nofollow
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Re: Increase ester count with Hydrochloric acid?

Post by johnnyv »

shaawnzee wrote:Yummyrum,

Yet another typo... No such thing as carbomate... But we are on the right track with carbamate! Yes, ethyl carbamate is carcinogenic.

It's found in all fermented things from urea and ethanol. Seems that heat is a major factor, ie, toasted bread has more than untoasted.

Doesn't appear a lower pH plays a detrimental role however. Found this:

"For example, lowering the temperature during fermentation and storage, lowering the pH, lowering the ethanol content, and adding diammonium phosphate as a supplement minimize the EC concentration. However, most of these techniques are performed as auxiliary preventive methods, and some are even impossible to achieve in practical fermentation situations (Zhao and others 2013a). "

I encourage all interested to look at table4 (Methods to decrease ethyl carbamate in those fermented beverages whose main precursor is cyanic acid).

https://onlinelibrary.wiley.com/doi/ful ... 4337.12084" onclick="window.open(this.href);return false;" rel="nofollow
Ethyl carbamate has a boiling point between 182 to 185 °C, not to mention in the presence of a strong acid like HCl or sulfuric it will likely be in NH3+ form meaning it would be vastly lower volatility.
This just doesn't seem to be a very relevant issue.
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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Think I might just need to bite the bullet and give it a go :)
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Re: Increase ester count with Hydrochloric acid?

Post by Yummyrum »

vqstatesman wrote:Think I might just need to bite the bullet and give it a go :)
Nothing gained , nothing lost .... as they say ....

Keep your safety glasses on and add acid . ... go for it vqstatesman
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Re: Increase ester count with Hydrochloric acid?

Post by Saltbush Bill »

Or is that nothing ventured , nothing gained ?
vqstatesman wrote:Think I might just need to bite the bullet and give it a go :)
Very interested to see the results of this ......can we have progress reports .... difference in smells straight off the still ....difference in taste and smell after a month on oak ...so forth n so forth.
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Re: Increase ester count with Hydrochloric acid?

Post by vqstatesman »

Thanks for all the input and comments. For me it's grain season for the next few months, mashing and distilling all on grain bourbon.

When I get back into doing Rum in a few months I will report back.
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Re: Increase ester count with Hydrochloric acid?

Post by Yummyrum »

Saltbush Bill wrote:Or is that nothing ventured , nothing gained ?
.
:oops: ... yeah that one Salty :D
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